Winchester KY Real Estate & Homes for Sale

114 Properties Found

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,234
Status:
Active
MLS#:
25505013
Type:
Single Family
Subdivision:
Colby Ridge
Lot size:
0.11 Acres
Year built:
2010
A broker reciprocity listing Courtesy: Real Broker LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

Completely renovated and move-in ready! This 3-bedroom, 2-bath home offers 1,234 sq. ft. of stylish living with beautiful hardwood floors, fresh finishes, and a bright open layout. The vaulted ceiling in the main living area adds space and light, while the updated kitchen features modern cabinetry and new appliances. Both bathrooms have been tastefully redone, and every detail reflects quality craftsmanship. Enjoy a comfortable backyard, convenient location, and true turnkey condition - perfect for first-time buyers or anyone seeking a low-maintenance home that feels brand new.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,636
Status:
Active
MLS#:
25504889
Type:
Single Family
Subdivision:
Calmes Estates
Lot size:
0.24 Acres
Year built:
1989
A broker reciprocity listing Courtesy: Dream Maker Realty, LLC 859-404-3384
View additional info

ADDITIONAL INFORMATION

Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half modern bathrooms *Located just minutes from the Winchester Bypass *Close to golf courses, shopping centers, and dining options Enjoy the perfect blend of comfort and convenience in one of Winchester's most desirable communities.

Beds:
5
Baths:
5.00
Sq.Ft.:
6,284
Status:
Active
MLS#:
25504793
Type:
Single Family
Subdivision:
Rural
Lot size:
12.81 Acres
Year built:
2022
A broker reciprocity listing Courtesy: The Agency 859-285-0614
View additional info

ADDITIONAL INFORMATION

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 approximately an 8-minute drive to Hamburg as well as 8-minute drive to downtown Winchester. 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.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,904
Status:
Active
MLS#:
25504530
Type:
Single Family
Subdivision:
Rural
Lot size:
7.27 Acres
Year built:
1998
A broker reciprocity listing Courtesy: United Real Estate Bluegrass 859-800-7355
View additional info

ADDITIONAL INFORMATION

Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring hardwood floors, a spacious living area, dining area and kitchen with granite countertops, an island and plenty of room for a breakfast table. Off the kitchen you have a large walk-in pantry, separate utility closet and oversized laundry room. The primary suite on the main floor offers convenience and luxury with a walk-in shower, whirlpool tub, double vanities, and generous walk-in closet. Upstairs you'll find a bedroom with ensuite, and three additional bedrooms, all with hardwood floors, three feature cedar-lined walk-in closets—perfect for storage and organization. Outdoor living shines here. Spend summers relaxing by the private swimming pool, enjoy peaceful evenings on the large back deck, have a fire around the firepit and enjoy the sunsets on the covered front porch. For hobbyists, horse lovers, small farm enthusiasts, or anyone needing serious storage and workspace, this property truly delivers: a 40' x 60' metal building with 14' x 16' garage doors, plumbed for a future bathroom and hookup for your RV, a 61' x 20.5' run-in shed with two stalls, a 10' x 40' barn, an additional storage shed, multiple paddocks, ideal for goats, horses, or small farm animals. Whether you're looking for privacy, a hobby farm, a place for your animals, or a home with room to roam, this property checks every box. With space, function, and beauty inside and out, you do not want to wait to schedule your private showing. Opportunities like this don't come around often—come experience it for yourself!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,521
Status:
Active
MLS#:
25504354
Type:
Single Family
Subdivision:
Rural
Lot size:
0.5 Acres
Year built:
1955
A broker reciprocity listing Courtesy: Coldwell Banker McMahan 859-744-1400
View additional info

ADDITIONAL INFORMATION

Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just minutes from town.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,966
Status:
Active
MLS#:
25504199
Type:
Single Family
Subdivision:
Wayland Heights
Lot size:
0.51 Acres
Year built:
1980
A broker reciprocity listing Courtesy: EXP Realty, LLC 888-624-6448
View additional info

ADDITIONAL INFORMATION

This charming 3-bedroom, 2-bath split level home offers the perfect blend of comfort and convenience-located just minutes from Lexington's popular Hamburg area with endless shopping, dining and entertainment options right at your fingertips! Step inside to find a beautifully updated kitchen featuring brand-new granite countertops and a stylish new island, perfect for family meals or entertaining guests. The spacious lower level provides the ideal spot to relax and enjoy Sunday football games or movie nights. Outside, you'll fall in love with the large backyard- a great space to create your very own outdoor oasis. Whether it's grilling out, gardening, or simply unwinding after a long day, this yard has the potential to be your private retreat. Don't miss this opportunity to own a home in a fantastic location that truly has it all!!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,046
Status:
Active
MLS#:
25503492
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.17 Acres
Year built:
1945
A broker reciprocity listing Courtesy: Woods Realty Group 859-644-5077
View additional info

ADDITIONAL INFORMATION

Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to month so the tentant is aware they will need to vacate the property before close of sale.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,260
Status:
Active
MLS#:
25503412
Type:
Single Family
Subdivision:
Saddle Brook
Lot size:
0.39 Acres
Year built:
1998
A broker reciprocity listing Courtesy: RE/MAX Creative, Winchester 859-422-2000
View additional info

ADDITIONAL INFORMATION

Charming 3 Bedroom Home with Vaulted Ceilings and Wooded Views Welcome to this inviting 3-bedroom, 2-bath home offering an open-concept layout filled with natural light and soaring vaulted ceilings. The spacious living area flows seamlessly into the kitchen and dining spaces—perfect for both everyday living and entertaining. Enjoy peace of mind with a brand-new HVAC system, Gutter guards and relax outdoors on the newly built deck, complete with a convenient ramp for easy access. The fenced area is ideal for a small dog, and the property backs to a beautiful wooded area with a picturesque stone wall, adding privacy and charm. Located in a quiet, established neighborhood, this home combines comfort, convenience, and a touch of nature—all in one perfect package.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,531
Status:
Active
MLS#:
25503339
Type:
Single Family
Subdivision:
Rural
Lot size:
5.02 Acres
Year built:
1950
A broker reciprocity listing Courtesy: RE/MAX Creative, Winchester 859-422-2000
View additional info

ADDITIONAL INFORMATION

Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character on cozy days, and the kitchen feels straight out of an HGTV show with a new island and a layout designed for cooking, gathering, and entertaining. The bedrooms offer multiple closets, and the full bath includes a convenient laundry space. A formal living room at the front of the home provides extra flexibility for a home office or sitting area. Outside, a large multi-level deck wraps from the side of the home around to the back, creating the perfect setting for outdoor dining or quiet mornings with coffee. The 5 acre property has a large clearing behind the house, offering space for a pool, garden, or play area, while the rest of the land is wooded and gently sloped, offering privacy and a scenic backdrop. There are already two raised garden beds and a spot for a fire pit in the side yard, plus a detached garage, chicken coop, and storage shed. The HVAC system is brand new, and the roof is only two years old. This property has been well cared for and thoughtfully upgraded over the years. Come see why this farmhouse could be your perfect country retreat!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,346
Status:
Active
MLS#:
25503252
Type:
Single Family
Subdivision:
Rolling Acres
Lot size:
0.19 Acres
Year built:
1960
A broker reciprocity listing Courtesy: Freedom Realty & Property Management 859-771-0777
View additional info

ADDITIONAL INFORMATION

ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,484
Status:
Active
MLS#:
25506124
Type:
Single Family
Subdivision:
College Park
Lot size:
0.13 Acres
Year built:
1960
A broker reciprocity listing Courtesy: Steven D Adams Real Estate Services, LLC 859-744-1080
View additional info

ADDITIONAL INFORMATION

Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,904
Status:
Active
MLS#:
25503055
Type:
Single Family
Subdivision:
Wesleyan Park
Lot size:
0.19 Acres
Year built:
1960
A broker reciprocity listing Courtesy: Freedom Realty & Property Management 859-771-0777
View additional info

ADDITIONAL INFORMATION

Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden vegetables that will be ready for backyard entertaining. There is an oversized storage/tool shed, and a partially fenced back yard. The HVAC, water heater and Window World windows are less than 5 years old. Don't miss this one level home complete with an American Flag and Pole

Beds:
3
Baths:
2.00
Sq.Ft.:
2,250
Status:
Active
MLS#:
25503172
Type:
Single Family
Subdivision:
Westmeade
Lot size:
0.18 Acres
Year built:
1980
A broker reciprocity listing Courtesy: Dream Maker Realty, LLC 859-404-3384
View additional info

ADDITIONAL INFORMATION

Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-bedroom, 2 full bath split-level home featuring a cozy finished basement perfect for relaxing or entertaining. Enjoy both front and rear porches, ideal for morning coffee or evening gatherings. The spacious, fenced-in backyard offers privacy and room to play, garden, or unwind. Nestled in a quiet neighborhood just minutes from the Winchester Bypass, this home provides easy access to shopping, dining, and everyday conveniences—making it the perfect blend of comfort and location.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,776
Status:
Active
MLS#:
25502706
Type:
Single Family
Subdivision:
Mcclure Manor
Lot size:
0.36 Acres
Year built:
1997
A broker reciprocity listing Courtesy: 5.23 Real Estate 859-428-7960
View additional info

ADDITIONAL INFORMATION

Beds:
3
Baths:
2.00
Sq.Ft.:
1,305
Status:
Active
MLS#:
25502677
Type:
Single Family
Subdivision:
Victory Heights
Lot size:
0.12 Acres
Year built:
1955
A broker reciprocity listing Courtesy: Berkshire Hathaway de Movellan Properties 859-266-0451
View additional info

ADDITIONAL INFORMATION

Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional. Recent updates include an HVAC system less than 5 years old, offering peace of mind and energy efficiency. With tons of potential inside and out, this adorable home is move-in ready and waiting for your personal touch. A great opportunity for first-time homebuyers or investors looking for a solid, well-kept property in a convenient location. Don't miss out on this Winchester gem! Ask about a lease to Purchase.

Beds:
5
Baths:
2.00
Sq.Ft.:
2,082
Status:
Active
MLS#:
25502349
Type:
Single Family
Subdivision:
Lyndale
Lot size:
0.19 Acres
Year built:
1969
A broker reciprocity listing Courtesy: Thwaites Realtors LLC 859-987-9119
View additional info

ADDITIONAL INFORMATION

**Open House Sunday 11/16 1-3PM** Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022, and exceptional curb appeal and charm, this home is just waiting for its new owner!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,747
Status:
Active
MLS#:
25502273
Type:
Single Family
Subdivision:
Oak Hill
Lot size:
0.34 Acres
Year built:
1994
A broker reciprocity listing Courtesy: Bridgewater Real Estate 859-745-8632
View additional info

ADDITIONAL INFORMATION

Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looking for. Formerly home to the beloved 2 Momma's Cooking for You, the property features a fully equipped commercial-grade kitchen with a separate entrance through the garage and rear of the home—perfect for culinary entrepreneurs, serious home chefs, or anyone who loves to host. Inside, you'll find two spacious living areas, a dedicated dining room, and an eat-in kitchen that brings everyone together. All four bedrooms are located upstairs, including a remodeled primary suite with a walk-in closet and updated bathroom. Whether you're entertaining guests on the screened-in back porch or enjoying the large flat backyard with family and friends, this home invites you to create the kind of memories that matter. From holiday dinners to summer cookouts, from quiet mornings to bustling evenings, this is a place where life happens—and where you'll be proud to call home.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,105
Status:
Active
MLS#:
25502189
Type:
Single Family
Subdivision:
Greenfield
Lot size:
0.55 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Keller Williams Legacy Group 859-544-6175
View additional info

ADDITIONAL INFORMATION

Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a renovated eat-in kitchen with a large island, leathered granite countertops, stainless steel appliances, and a gas range. A spacious walk-in pantry adds functionality, while updated windows, recessed lighting, and a new slider door (2025) bring in natural light. The primary suite is a true retreat with a private bath and an expansive walk-in closet. On the opposite wing, you'll find a second primary suite, creating the perfect setup for multi-generational living or hosting long-term guests. Outside, the property continues to impress with two driveways for ample parking, a large usable yard, and a huge detached garage ideal for parking, storage, or a workshop. An updated storage shed (2025) adds even more utility.

Beds:
6
Baths:
4.00
Sq.Ft.:
3,544
Status:
Active
MLS#:
25501793
Type:
Single Family
Subdivision:
Rural
Lot size:
0.19 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Tru Life Real Estate 859-785-1986
View additional info

ADDITIONAL INFORMATION

Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future expansion. A detached 2-car garage provides ample parking. This is a fantastic opportunity for investors—whether you're looking for strong rental income or a place to call home while renting out the other unit.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
25501640
Type:
Single Family
Subdivision:
Plantations
Lot size:
0.24 Acres
A broker reciprocity listing Courtesy: Keller Williams Legacy Group 859-544-6175
View additional info

ADDITIONAL INFORMATION

Here is the Blank Canvas to build your Dream Home in the Plantation Subdivision. This two story brick building, formerly the Sales Office for the Subdivision, has been gutted to offer the unique opportunity to build a 3118 Sq Ft Home consisting of Four Bedrooms, Two and Half Baths, an open concept on the main level with the addition of a two car garage. Contact listing agent to discuss current plans and renderings for completion of build-out. Close to I-64, shopping, stores, and Industrial Park.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,311
Status:
Active
MLS#:
25501816
Type:
Single Family
Subdivision:
Rural
Lot size:
7.4 Acres
Year built:
2003
A broker reciprocity listing Courtesy: RE/MAX Elite Lexington 859-245-1165
View additional info

ADDITIONAL INFORMATION

This beautiful home sits on over 7 acres of peaceful countryside. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of your outdoor toys. The detached garage has water and electrical service with a workshop area and also a large unfinished loft area for additional storage which could be converted into an apartment. The lovely custom home with over 3300 square feet has hardwood flooring throughout, crown molding, tall ceilings, and built in shelving in the family room. Lots of natural light in the living area with the sunburst arched windows overlooking the property. The home has a convenient split bedroom concept. The spacious primary bedroom has an ensuite bath with a soaking tub and separate vanities and a large closet. The upstairs has an additional full bathroom with 2 large flex rooms with one currently being used as a 4th bedroom. The additional flex room would be a great recreation room or maybe additional storage. This well-maintained country home offers the convenience of Winchester shopping and dining and also only 8 miles to I64 and I75. If you have been looking for a home with a quiet country setting this is the perfect property.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,604
Status:
Active
MLS#:
25501469
Type:
Single Family
Subdivision:
Beaumont Terrace
Lot size:
0.29 Acres
Year built:
2010
A broker reciprocity listing Courtesy: The Brokerage 859-983-7365
View additional info

ADDITIONAL INFORMATION

Come see this immaculate 3 bedroom, 2 bath single-story ranch with an open-concept split bedroom layout and 1,604 square feet of living space. This home has been beautifully maintained and is ready for its next owner. Inside you will find laminate and tile floors and stainless steel appliances that make daily living easy and stylish. The spacious design flows seamlessly, creating a bright and welcoming atmosphere. Step out back to a patio and deck with an above-ground pool, perfect for entertaining friends and family. The backyard also features two well-kept storage sheds, offering plenty of space for tools and outdoor gear. A well-maintained storm shelter as well as a new water heater adds extra peace of mind. Call today to schedule your private showing.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,254
Status:
Active
MLS#:
25501100
Type:
Single Family
Subdivision:
Lincoln Park
Lot size:
0.27 Acres
Year built:
1991
A broker reciprocity listing Courtesy: Keller Williams Bluegrass Realty 859-260-1444
View additional info

ADDITIONAL INFORMATION

Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop now.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,170
Status:
Active
MLS#:
25501136
Type:
Single Family
Subdivision:
Rural
Lot size:
10 Acres
Year built:
1977
A broker reciprocity listing Courtesy: ERA Select Real Estate 859-296-1525
View additional info

ADDITIONAL INFORMATION

Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from the covered front porch, the perfect spot for rocking chairs and morning coffee, or from the large back deck, ideal for entertaining, cookouts, or quiet evenings overlooking your land. Practical features include a 1-car attached garage for everyday convenience and a 2-car detached garage, providing plenty of space for storage, a workshop, or hobbies. Outside is where this property truly shines. With 10 rolling acres, you'll have room to roam, garden, raise animals, or simply soak in the wide-open skies. Imagine watching wildlife wander across your land or ending the day with a peaceful sunset over the trees. Tucked away yet conveniently close to Winchester and just a short drive to Lexington, this property is the perfect blend of seclusion and accessibility. Whether you're dreaming of a small homestead, weekend getaway, or just a quieter way of life, this home is ready for you!

Beds:
4
Baths:
4.00
Sq.Ft.:
4,345
Status:
Active
MLS#:
25500860
Type:
Single Family
Subdivision:
Rural
Lot size:
8.33 Acres
Year built:
2003
A broker reciprocity listing Courtesy: Keller Williams Commonwealth 859-721-2121
View additional info

ADDITIONAL INFORMATION

Move into INSTANT equity Listed BELOW appraisal! This 4bd 4bath home has 2 BONUS ROOMS, a pool PLUS an attached and detached garage with finished space! This is a MUST see! Your dream country retreat awaits! Nestled on 8+ scenic acres, this stunning brick ranch offers the perfect blend of modern efficiency, functional living space, and peaceful country charm. A brand-new geothermal heating and cooling system ensures year-round comfort and energy savings, giving you confidence in your home's efficiency for years to come. The main level boasts a spacious primary suite, two additional bedrooms, and a formal dining room, ideal for both family gatherings and everyday living. A heated and cooled all-seasons sunroom provides the perfect spot to sip morning coffee or unwind in the evenings while enjoying the tranquil views of the surrounding landscape. The finished walkout basement expands the living space with a private bedroom, full bath, wet bar, and two versatile bonus rooms that can serve as a home gym, playroom, or office. A fireproof den offers secure space for a safe or valuables, while the basement walkout leads directly to a concrete pad—an ideal setup for a Jacuzzi or outdoor seating with easy backyard access. Step outside and enjoy your own private oasis with a sparkling saltwater in-ground pool, perfect for summer entertaining. An invisible fence is already in place, giving pets the freedom to explore the property safely. For parking, storage, and hobbies, this property truly excels. You'll find a total of four garage spaces plus two additional bays designed for riding mowers or equipment. The two-car attached garage is complemented by a detached, heated and cooled workshop featuring two garage bays, two bonus bays, and a finished loft. Whether you need space for a guest suite, home office, hobby area, or creative studio, this versatile setup has you covered. From its thoughtful interior layout to its outdoor amenities, this home delivers everything you need for comfort, functionality, and entertainment. With modern upgrades, generous space, and the serene backdrop of country living, this property is truly one of a kind—and ready for you to call home.

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Andrea D. Conner, License 221773, Xome Inc., License 239054, [email protected], 844-400-XOME (9663), 1795 Alysheba Way, Suite 102, Lexington, KY 40509


The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Lexington Bluegrass Multiple Listing Service. The Broker providing this data believes them to be correct but advises interested parties to confirm them before relying on them in a purchase decision. Copyright 2026 Lexington Bluegrass Multiple Listing Service. All rights reserved.



Winchester Real Estate

Winchester is located in Kentucky. Winchester, Kentucky has a population of 18,993. Winchester is less family-centric than the surrounding county with 25.63% of the households containing married families with children. The county average for households married with children is 25.74%.

The median household income in Winchester, Kentucky is $47,034. The median household income for the surrounding county is $59,294 compared to the national median of $69,021. The median age of people living in Winchester is 36.9 years.

Winchester Weather

The average high temperature in July is 85.8 degrees, with an average low temperature in January of 22 degrees. The average rainfall is approximately 45.8 inches per year, with 9.4 inches of snow per year.

Winchester Map

Winchester Real Estate Market Conditions

  • Median sales price

    $309,000
    19.3%
    change since last quarter
  • # Active listings

    201
    30-day change

Winchester Schools and Demographics

Education near Winchester, KY

City County
High School Graduates 86.63 89.23
College Degree - 2 year 8.6 9.97
College Degree - 4 year 19.04 20.05
Graduate Degree 4.07 5.81
Expenditures per Student 14,536 14,536
Students per Teacher 13.6 13.6

Elementary Schools near Winchester, KY

Grades Students P/T Ratio ZIP
Athens-Chilesburg Elementary School KG - 05 745 14.9 40509
Camargo Elementary School PK - 04 612 13.2 40353
Clark County Preschool PK - PK 296 24.7 40391
Clay City Elementary School PK - 05 535 16.7 40312
Mapleton Elementary School KG - 04 674 14.7 40353
Montgomery County Early Learning Center PK - PK 109 18.2 40353
Mount Sterling Elementary School KG - 04 635 15.1 40353
North Middletown Elementary School KG - 05 155 14.8 40357
Shearer Elementary School KG - 04 423 12 40391
Strode Station Elementary School KG - 04 613 12.4 40391
William G. Conkwright Elementary KG - 04 563 20 40391
Willis H. Justice Elementary School KG - 04 491 16.2 40391

Middle Schools near Winchester, KY

Grades Students P/T Ratio ZIP
Edythe Jones Hayes Middle School 06 - 08 1,095 15.6 40509
McNabb Middle School 07 - 08 718 16.2 40353
Mercer County 9th Grade Academy 09 - 09 224 16.2 40391
Montgomery County Intermediate School 05 - 06 712 15.6 40353
Rev. Henry E. Baker SR. Interm. School 05 - 06 858 19.5 40391
Robert D. Campbell Jr. High 07 - 08 801 18.2 40391
Willis H. Justice Elementary School KG - 05 0 13.7 40391

High Schools near Winchester, KY

Grades Students P/T Ratio ZIP
George Rogers Clark High School 09 - 12 1,672 18.2 40391
Montgomery County High School 09 - 12 1,338 18.4 40353

Ungraded Schools near Winchester, KY

Grades Students P/T Ratio ZIP
* Gateway Children's Services 07 - 12 18 9 40353
* Hillcrest Hall Treatment Center 09 - 12 12 12 40353
* Phoenix Academy 07 - 12 22 4.4 40391
* The Sterling School 09 - 12 51 11.3 40353
Clark County Area Technology Center UG - UG 0 40392
Hayes Pre-School UG - UG 93 30.5 40509
Montgomery County Accelerated Academy UG - UG 0 40353
Montgomery County Area Technology Center UG - UG 0 40353

Demographics near Winchester, KY

City County
Neighborhood Type Suburban
Population 18,993 36,716
Population Density 2,078 145
Median Age 36.9 41.5
People per Household 2.3 2.5
Median Household Income 47,034 59,294
Average Income per Capita 28,337 33,205

Real estate near Winchester