Winchester KY Real Estate & Homes for Sale

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Beds:
4
Baths:
4.00
Sq.Ft.:
4,665
Status:
Active
MLS#:
24018605
Type:
Single Family
Subdivision:
Rural
Lot size:
1.64 Acres
Year built:
1993
A broker reciprocity listing Courtesy: Freedom Realty & Property Management 859-771-0777
View additional info

ADDITIONAL INFORMATION

Recent price reduction has this home price at $139 per finished square foot. This is not counting extra basement space and attic space. When you enter this amazing custom-built home, you will feel at home. A multitude of incredible amenities, it's hard to even know where to start, we will begin in the kitchen that received a massive update in 2020 that included quartz countertops and backsplash, some new cabinets, new flooring, as well as new lighting and appliances. Next let's move to the basement that features an amazing entertainment area that has an overhead projector and large screen for family movie nights. You can enjoy your morning coffee on the beautiful covered back patio with brick walls and posts that overlooks a big back yard and a pond that's on the adjoining property making you feel as if you are deep in the country instead of being a little over a mile from the bypass. You will notice the plumbing and electric has been completed to a high-level in this home. 4,600 sq. ft finished plus 900 unfinished in basement and 800 in floored attic. All information is believed to be accurate. Buyer to confirm.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,526
Status:
Active
MLS#:
24018474
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.15 Acres
Year built:
1930
A broker reciprocity listing Courtesy: Woods Realty Group 859-644-5077
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ADDITIONAL INFORMATION

Charm meets convenience in this delightful newly renovated home! Experience city living at its finest with the tranquility of your own spacious backyard, yet be within walking distance to shops and restaurants! Step inside the living room and let the natural light peeking through the large windows welcome you home. With a bedroom on the main floor, two bedrooms upstairs, and a bonus room that can be used however you desire, this home would be perfect for a growing family!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,635
Status:
Active
MLS#:
24018286
Type:
Single Family
Subdivision:
Creekside
Lot size:
0.23 Acres
Year built:
2024
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75, Lexington, Richmond, shopping, churches, hospital and schools, pictures to follow as home is being constructed.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,600
Status:
Active
MLS#:
24017675
Type:
Single Family
Subdivision:
Creekside
Lot size:
0.42 Acres
Year built:
2024
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

Don't miss out on this wonderful ranch floor plan, New Construction, 3 bedrooms, 2 baths, covered porch, great location, Call today.Size of home may vary from plan, spec home,all specifics have already been ordered. This information will follow within a few weeks and posted on line.

Beds:
2
Baths:
1.00
Sq.Ft.:
972
Status:
Active
MLS#:
24017233
Type:
Single Family
Subdivision:
Thomson Addition
Lot size:
0.23 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

You must view this adorable remodeled home located in a convenient location, charming, large back yard, walk to downtown Winchester, close to college park, make sure you view this one today! Sentri lock is on the back door, parking in rear allley access

Beds:
4
Baths:
4.00
Sq.Ft.:
3,200
Status:
Active
MLS#:
24016751
Type:
Single Family
Subdivision:
Thomson Addition
Lot size:
0.27 Acres
A broker reciprocity listing Courtesy: RE/MAX Creative, Winchester 859-422-2000
View additional info

ADDITIONAL INFORMATION

As you enter the colonial-style home, you're met with a foyer that sets the tone for the home's timeless charm. The welcoming floor plan invites you to the formal dining room or great room on each side, perfect for hosting. The kitchen features beautiful custom-built maple cabinets. Continue into the cozy living room & breakfast nook, where French doors open to a screened-in porch & an expansive deck, providing the perfect spot for enjoying morning coffee. Off the great room, you'll find the first of two primary bedroom suites.. The second is on the second floor, complete with a kitchenette for convenience. Also you'll find a third full bath, a bedroom with a large custom-built armoire and a 4th bedroom that being used as a laundry room. The nearly 1200 sqft basement holds incredible potential, featuring a fireplace & kitchenette. Whether you envision it as additional living space or a vast storage area, this clean & dry basement is a blank canvas ready for your ideas. With its generous room sizes and top-quality craftsmanship, this home offers both luxury and practicality in the heart of Winchester's historic Thomson Additio

Beds:
6
Baths:
4.00
Sq.Ft.:
5,227
Status:
Active
MLS#:
24016037
Type:
Single Family
Subdivision:
Stoneybrook
Lot size:
0.43 Acres
Year built:
1993
A broker reciprocity listing Courtesy: Dream Maker Realty, LLC 859-404-3384
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ADDITIONAL INFORMATION

Discover your dream home with this expansive 6 bedroom, 3.5 bath haven.The main floor boasts a primary en-suite, office space, and laundry room, while the second floor offers additional bedrooms and a versatile bonus room. The basement offers private bed/bath, custom bar, home theater, infrared sauna and home gym. Step outside and prepare to be enchanted by an outdoor oasis. Outdoor kitchen complete with Big Green Egg and gas fireplace. The crown jewel of this outdoor space... the stunning 18x36 Grecian In-ground pool accompanied by a custom stone gas fire pit. Whether you're binging the latest blockbuster in the home theatre or enjoying a serene morning by the pool, this home offers a blend of relaxation and entertainment. This residence isn't just a place to live; it's a place to thrive and create unforgettable memories. Ready to dive into your new lifestyle? Your dream home awaits!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,564
Status:
Active
MLS#:
24015318
Type:
Single Family
Subdivision:
Boonesboro
Lot size:
1.18 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Hunter Real Estate 859-312-6366
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ADDITIONAL INFORMATION

Home features living room, kitchen, dining area, bonus room, primary bedroom with adjoining bath on main level, upstairs has two additional bedrooms, full bath and another bonus room with large closet and separate exterior entrance. Home has Large detached garage (over 1500 sq ft per pva) .Home sq ft and lot size per pva and are not warranted. Hold Harmless must be signed before entering.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,261
Status:
Active
MLS#:
24015067
Type:
Single Family
Subdivision:
Hampton Manor
Lot size:
0.33 Acres
Year built:
1960
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

Beautiful Hampton Manor home offers easy access to all Winchester has to offer! Located right off Boone Ave, this home boasts tons of updates including an Entertaiment Kitchen with granite countertops, Bosch appliances and great storage, refinished hardwoods, new windows, Updated bathroom showers, a pool, covered front porch back porch and separate covered area outback to enjoy all summer long. 3 Bedrooms on the main level including a primary suite with 2 closets, 2 guest bedrooms, and full guest bathroom. Beautiful living room with gas log updated fireplace, a Den with Gas logs and an enclosed all-season room! A full walk out basement with oversized 2 car garage, 1/2-bathroom, Game Room or office with another updated fireplace with gas logs, laundry room and great closet storage!!! Move in a truly enjoy the beautiful yard, landscaping and just relax!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,148
Status:
Active
MLS#:
24014457
Type:
Single Family
Subdivision:
Hampton Manor
Lot size:
0.31 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Rector Hayden Realtors 859-276-4811
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ADDITIONAL INFORMATION

Charming Home in Hampton Manor!... Welcome to Hampton Manor, one of Winchester's top neighborhoods! This beautifully maintained home, loved by the same owner for 32 years, is now seeking a new owner to appreciate its charm and prime location near the Winchester Country Club. Step inside to a bright Living Room with triple windows, hardwood floors, and a cozy gas log fireplace. The dining area design flows into a remodeled Kitchen with high-end Custom Mouser Cabinetry, an island with butcher block, and stunning granite countertops. The kitchen features under-cabinet lighting, a direct vent hood, and stainless-steel appliances. The unique Dutch door leads to a covered porch and two TREX composite decks, perfect for outdoor relaxation. The main level includes a primary bedroom suite with vaulted ceilings, hardwood floors, private deck access, and an ensuite bath with a large shower. Two additional bedrooms and a main bathroom complete this level. The partially finished basement offers a versatile space with a wood-burning fireplace, ideal for a Rec Room or Family Room. The bright laundry area and expansive unfinished space provide endless possibilities, from workshops to

Beds:
4
Baths:
1.00
Sq.Ft.:
2,327
Status:
Active
MLS#:
24013805
Type:
Single Family
Subdivision:
South Park Addition
Lot size:
0.18 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Dream Maker Realty, LLC 859-404-3384
View additional info

ADDITIONAL INFORMATION

162 French Ave, Winchester, Kentucky, is a charming residential property located in a quiet neighborhood. The house is a single-family home, 2,327 square feet, with a beautiful front porch perfect for enjoying the Kentucky weather. The property features a well-maintained lawn adding to its curb appeal.As you approach the front door, you'll notice the classic design with large windows allowing natural light to brighten the interior. The interior of the house is spacious and thoughtfully laid out.The bedrooms are comfortable and provide a relaxing retreat after a long day. The backyard of the property is a peaceful oasis.Overall, 162 French Ave is a lovely home that offers both comfort and style, making it a wonderful place to live in Winchester, Kentucky. Inspections are welcome but owner will not do any repairs.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,908
Status:
Active
MLS#:
24013815
Type:
Single Family
Subdivision:
Holiday Hills
Lot size:
0.52 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

Once you come in you won't leave, this sprawling ranch with a nice back yard just waiting for you, 4 bedrooms, 3 full baths, this home has the perfect spot for a garden, family size lawn, corner lot, Some hardwood floors, fireplace, close to town, church, schools, hospitals, shopping, Lexington, Richmond, call today!

Beds:
5
Baths:
6.00
Sq.Ft.:
5,498
Status:
Active
MLS#:
24013378
Type:
Single Family
Subdivision:
Downtown
Lot size:
4 Acres
Year built:
1965
A broker reciprocity listing Courtesy: Coldwell Banker McMahan 859-744-1400
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ADDITIONAL INFORMATION

Discover unparalleled elegance with no detail left unturned, nestled on 4 acres in the heart of Winchester. This exquisite property spans 5400 sq feet & offers 5 bedrooms, 3 full baths & 3 half baths, ideal for gracious living & entertaining. Step into a gourmet kitchen with two expansive islands, perfect for culinary enthusiasts. Enjoy the serene ambiance of a beautiful sunroom, offering relaxation & panoramic views of the grounds. Experience true outdoor living with an impressive array of amenities. Entertain effortlessly with an outdoor kitchen, while the inground pool & trampoline provide recreation & relaxation for all. Impeccably designed & maintained, this home combines luxury with everyday comfort, offering a lifestyle of tranquility & sophistication! home currently has a contract with a 24hr kickout.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,770
Status:
Active
MLS#:
24013314
Type:
Single Family
Subdivision:
Mallard Cove
Lot size:
0.38 Acres
Year built:
2022
A broker reciprocity listing Courtesy: McCormick Realty Inc. 859-498-4317
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ADDITIONAL INFORMATION

WOW! Exceptional! Attention to detail was clearly taken in the building of this stunning home. Entrance foyer leads to the living rm w/stone gas log fireplace, kitchen and dining rm. Coffered ceiling w/ceiling fan, quartz countertops, backsplash, convection oven w/glass cook top, walk in pantry w/custom cabinets. Primary suite w/tray ceiling, split vanities, walk-in shower, spa-like tub, private toilet and the huge, custom walk-thru closet that leads to utility rm. On the other side of the house are three additional bedrooms and full bath. Half bath off the kitchen area. Upstairs offers a finished bonus rm. So many extra touches have already been completed saving you the time and effort and include crown molding thru-out, tile floors in baths, light/fan remotes, custom blinds. French doors open to the beautiful porch and the heated pool where you will relax & entertain! Beautiful fencing around pool area. The large 2 car attached garage w/high ceiling offers plenty of storage space. Plus the detached garage (400 sf) has c/h/a & a dog wash area. Move right on in and take a dip in the beautiful 5' heated pool with colored lights. Beautiful New Subdivision with a private lake.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,091
Status:
Active
MLS#:
24013072
Type:
Single Family
Subdivision:
Hampton Manor
Lot size:
0.61 Acres
Year built:
1958
A broker reciprocity listing Courtesy: Coldwell Banker McMahan 859-744-1400
View additional info

ADDITIONAL INFORMATION

This is rare beauty and history located in the heart of Winchester. Embrace the essence of elegance in this beautifully appointed brick home, offering 5 bedrooms, 3 full baths and formal rooms. Main level of home boasts the primary suite as well as an additional bedroom. The large fully equipped kitchen is a delight for any chef. Home features a full walk-up basement that is unfinished with a half bath and additional laundry area. This home nestled on a spacious lot with a serene brick patio inviting relaxation. The 2 car carport situated close to home with plenty of storage.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
24012327
Type:
Single Family
Subdivision:
Plantations
Lot size:
0.24 Acres
A broker reciprocity listing Courtesy: Keller Williams Bluegrass Realty 859-260-1444
View additional info

ADDITIONAL INFORMATION

OPEN HOUSE! THIS SATURDAY June 29th 12-3PM! 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:
2
Baths:
1.00
Sq.Ft.:
1,116
Status:
Active
MLS#:
24009464
Type:
Single Family
Subdivision:
Rural
Lot size:
5 Acres
Year built:
1950
A broker reciprocity listing Courtesy: Keller Williams Legacy Group 859-544-6175
View additional info

ADDITIONAL INFORMATION

Embrace the potential of this 5-acre gem near Winchester and Hamburg, KY. Located in beautiful Clark County, this fixer-upper boasts 2 bedrooms, 1 bath, and scenic farm views on flat, versatile land perfect for building or farming. The property features a long driveway and a detached 2-car garage, ideal for creating a smaller homestead. Enjoy the tranquility of country living with the convenience of being just a short drive from Lexington, offering a blend of urban and rural experiences.Clark County is known for its rich history, friendly communities, and picturesque landscapes. With its proximity to the vibrant city of Lexington, you can explore cultural attractions, shopping, dining, and entertainment. Living in Kentucky means experiencing the charm of the Bluegrass State, renowned for its horse farms, bourbon distilleries, and outdoor recreational opportunities. This property offers a unique blend of privacy and accessibility to amenities, making it an excellent opportunity for those looking to embrace a rural lifestyle with city conveniences. Come check it out!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,422
Status:
Active
MLS#:
24007633
Type:
Single Family
Subdivision:
Sunset Heights Addit
Lot size:
0.17 Acres
Year built:
1961
A broker reciprocity listing Courtesy: Milton and Associates Real Estate 859-983-9045
View additional info

ADDITIONAL INFORMATION

This three bedroom Ranch home has one and 1/2 baths,a large family room with a fireplace, has been updated, new flooring, new interior and exterior painting,New HVAC, new kitchen cabinets with grainte, new appliances ,It also has a large work shop.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,215
Status:
Active
MLS#:
23023763
Type:
Single Family
Subdivision:
Forest Park
Lot size:
0.2 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Ensor Real Estate, LLC 859-749-0892
View additional info

ADDITIONAL INFORMATION

Great All Brick Ranch offers 4 bedrooms, 1.5 bathrooms, Spacious Kitchen, Nice Living Room, Laundry Room, Hardwood flooring, Great closet space, move in ready easy one level living! Beautiful Magnolia Trees, and a Storage shed out back! New Gutters 2024!

Beds:
4
Baths:
5.00
Sq.Ft.:
4,698
Status:
Active
MLS#:
24007462
Type:
Single Family
Subdivision:
Hampton Manor
Lot size:
2.6 Acres
Year built:
1885
A broker reciprocity listing Courtesy: Block + Lot Real Estate 859-309-0099
View additional info

ADDITIONAL INFORMATION

One of a kind opportunity to live in history and in luxury in one of Winchester's finest offerings. This majestic home spares no detail, offering charming details throughout like hardwood floors, high ceilings, large windows, crown moldings, and fireplaces throughout. As well, the gracious lot offers expansive views and privacy with its large patio seating area and beautiful swimming pool. Ripe for entertaining or just relaxing in the privacy of this incredible estate, this home is located ideally in the south side of Winchester, conveniently located a golf cart drive across the street from Winchester Country Club and a straight shot to Lexington in under 15 minutes. This home has been painstakingly maintained and updated. See enclosed for an expansive list of improvements made.

Beds:
4
Baths:
3.00
Sq.Ft.:
5,328
Status:
Active
MLS#:
23016936
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.38 Acres
Year built:
1814
A broker reciprocity listing Courtesy: Block + Lot Real Estate 859-309-0099
View additional info

ADDITIONAL INFORMATION

We are honored to present this rare opportunity to purchase a beautiful, historic property in the heart of Winchester, Kentucky. Built in 1814 and upon complete renovations in the 1980s and again the past 5 years, this property is a wonderful blend of historic charm with modern upgrades and high quality piece of mind. Zoned as P-1, it can function as a commercial property or as residential and the current configuration is already conducive to both as it sits today with features doubling as office/bedrooms, fully equipped kitchen, patio space, closets, 2.5 bathrooms. Other qualities include hardwood floors, fire places, high ceilings, large windows, second floor deck space, outdoor patio, large lawn and parking. Truly an oasis ripe for living, working, entertaining, or as an investment opportunity!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,150
Status:
Active
MLS#:
23007540
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.1 Acres
A broker reciprocity listing Courtesy: WTC Realty LLC 606-344-6560
View additional info

ADDITIONAL INFORMATION

Nestled in the charming town of Winchester, Kentucky, this 1,150 sq ft home offers the perfect blend of character and potential. Though it may require some repairs, this property boasts an abundance of possibilities for the savvy buyer.

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76–97 of 97 properties displayed
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 2025 Lexington Bluegrass Multiple Listing Service. All rights reserved.



Winchester 40391 Real Estate

Winchester is located in Kentucky. Winchester, Kentucky 40391has a population of 18,993. Winchester 40391 is less family-centric than the surrounding county with 25.5% 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 40391 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 40391 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

    N/A
  • # 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
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 40391

Zip Code City
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